He Remembers the First Times
by superdupersk8r61
Summary: Changed to a TwoShot! Jackson remembers some of the firsts in his life. And they all have to do with a certain girl...who just happens to be his little sister's best friend. JacksonXLilly. Please Read and Review!
1. Chapter 1

**A/N: **Hey all! This is my first Hannah Montana fic! It's just something that got stuck in my head last night and it wouldn't go away until I wrote it down. I would love to hear what you guys think. Please Read and Review! Oh, and the majority of it is written in italics because it's mostly flashbacks. And again, reviews are appreciated!! ;)

**Disclaimer: **Obviously, I don't own anything to do with "Hannah Montana". But I have to say it anyway. So I did.

* * *

**He remembers the first time he met her.**

_13 year-old Jackson at on the couch in his new home in Malibu. It was the afternoon after his first day in his new school, and already he had more homework than he ever did at his school in Tennessee. _

_He heard a car pull up in the driveway, his dad coming home after picking up his 10 year-old sister, Miley, from her new school._

_"Jackson, we're home!" his dad, Robby-Ray, hollered as he barged into the house._

_"I'm right here, Dad," he called back from the couch, about 5 feet away from the door._

_Miley bounded into the house, and following behind here was a little girl, with long, flowing blonde hair. _

_"Hey, Jackson. This is my new friend, Lilly. I met her at school today," his sister told him excitedly. _

_He grunted a "hello" with disinterest, and turned his attention back to his algebra homework. However, he felt a pair of eyes on him. He looked up and found his sister's friend staring at him intently. _

_He was patient for a few minutes, but when she did not break her gaze he asked, "Can I help you?"_

_"Do you know who you look like?" the little girl asked him. "You look like Simba from the Lion King."_

_Miley erupted with giggles, as did her friend. Jackson's eyes got wide with offense, and he jumped off the couch. The girls took off, running throughout the house, with him close behind._

**He remembers the first time he actually felt something when he saw her.**

_He sat in the kitchen while his dad made dinner. Miley and Lilly were upstairs, getting ready for one of their school dances. He saw his sister come down the stairs, but she was alone._

_When Miley reached the bottom of the stairs, she turned around and hollered. "Lilly! Get down here!"_

_"I can't!" came the frantic reply._

_"Well, why not?"she yelled back._

_"I look ridiculous!" Lilly answered._

_"Don't be insane, Lilly, you look hot!"_

_When there wasn't a reply, Miley sighed in frustration. "That's it. I'm coming back up to get you!" and with that, she hurried back up the stairs._

_Jackson looked at his father questioningly. Robby-Ray could only shrug and mutter, 'Women."_

_He then heard two sets of footsteps coming down the stairs. Miley was in the front, quickly dragging a reluctant Lilly behind her. He indifferently looked up, and when he did, Lilly literally took his breath away. He began choking potato chip he had been eating. His face turned red, and his eyes teared up, as he coughed violently, waving his arms, trying to dislodge the pesky object._

_"What's with him?" Miley asked her father as she and Lilly joined them in the kitchen._

_"Miley, don't ask me to understand your brother," Robby-Ray said looking at Jackson, just in case his son really was in trouble._

_Jackson finally was able to force the chip down safely. He was not, however, able to tear his eyes off of Lilly. Clearly his sister had influenced her wardrobe choice that night. Which, was probably what made him look twice. Gone were her baggy shorts, oversized T-shirt, and standard funky hat. And in their places, were a denim mini-skirt, a lacy black cami, and her hair was piled on her head, with random blonde tendrils framing her face. His immediate thought was "Damn. She looks hot." But then he thought, "What am I doing? I can't be thinking these things. She's Lilly. Miley's friend. Miley's friend who annoyed the hell of him. Right? He wasn't sure, but looking at her, and for the first time, he realized she had grown up. And quite nicely too._

_"Doesn't Lilly look hot, Jackson?" his sister asked him, only trying to boost her friend's confidence, but her question had an effect on her brother too. _

_He started coughing again, but quickly changed it into a laugh, trying to mask his discomfort. "What, Lilly? Hot? That's crazy talk, Miles," he said, putting on a disgusted facade so she wouldn't know what he really thought._

_He didn't catch Lilly's crest-fallen look, but Miley did. "Don't worry, Lilly. Jackson wouldn't know hot if it hit him in the face. Come on, let's go to the dance."_

_And with that, the two girls left, leaving him thinking about his little sister's friend in a new light._

**He remembers the first time he was alone with her.**

_One night, he was sitting in the living room with his sister and Lilly watching a scary movie in the dark. He couldn't have been less scared, while the two girls clung to each other, terrified out of their minds. Suddenly, a monster appeared on screen and both girls screamed. The popcorn bowl they were holding between them went flying, and emptied its contents all over the floor._

_"Crap, now I gotta go get more popcorn," Miley said, getting up from the couch, to search the kitchen._

_She looked through every cabinet but her efforts were futile. "We're out. I'm gonna run to the store down the street. I'll be right back."_

_"Miley! You can't leave me here!" Lilly exclaimed, a worried expression on her face._

_"Don't worry. You've got Jackson," she said with a giggle, as she grabbed her jacket off the kitchen chair and ran out the door._

_Jackson was nervous. He had been steadily developing a crush on Lilly ever since he saw her on the night of her and Miley's dance. After that he started noticing the little things. How funny she was, and how cute it was when she came skateboarding through his front door. And now, here he was, alone with her. But he wasn't sure of what to do._

_Because it was dark in the room, he could look at her without her knowledge. He watched her as she focused on the screen, her eyes growing wide with every scary image. _

_Then next thing he knew, she let out a blood-curling scream, and somehow, she ended up in his lap. When she realized what she had done, she seemed embarrassed._

_"Oh, I'm sorry." she said, her face turning red as she slid off him._

_"Aww, was wittle Wiwwy a wittle scared?" he said, in a mocking baby voice to cover up the obvious pleasure he felt with her being so close to him._

_Lilly smacked him with a pillow. "I was not scared, exactly. Just a little...surprised," she said, trying to be tough._

_Jackson laughed. "Oh man. Was that the understatement of the year. That's like saying the Grand Canyon is just a little pothole," he joked._

_Lilly rolled her yes. "Whatever," and went back to the movie. However, in less the a minute, she found herself glued to Jackson's side, her head buried in his chest._

_Jackson didn't say anything and this time she made no apologies. His breathing increased as she pressed her body into his. He was taken by an overwhelming urge to run his fingers through her silky hair. His hand was poised above her head, about to do the deed, when his sister came back, crashing open through the door._

_Lilly's head sprang up from his chest, and she stealthily moved back down the couch to avoid any questions from Miley._

_Jackson's head fell back to the couch with a sigh. He had Lilly alone and hadn't done anything about it. She was always with Miley. He wasn't sure if he'd get this chance again. He felt like such a wuss._

**He remembers the first time his was questioned by his sister about her. **

_He was sitting on the back of the couch, playing video games when his sister came back from walking Lilly home. "JACKSON!" she shouted, flinging open the door and staying in the doorway. "Do you like Lilly?!"_

_Her question caught him by such surprise that he jumped. The video game controller flew out of his hands and up into the air, as he tumbled off the back of the couch and landed on the floor with a loud "THUD"._

_"Ouch," he moaned, rubbing his head in pain. _

_Miley ran over, and stood above him, looking down at her brother. "Well, do you?" she asked sternly, her hands on her hips. _

_He remained lying on floor. "What are you talking about?"he asked._

_She sighed loudly, and plopped down onto her brother, pining him down. "Don't even deny it. I saw you looking at her all day. Actually, in fact, you seem to be looking at her whenever she's here, which, you know, is pretty much all the time."_

_"I do not," he said earnestly, wiggling frantically, trying to get his sister off of him._

_"Oh, come on," she said to him, obvious that she didn't believe him. "You look at her like I look at Jake."_

_Miley had caught him, and he knew it. He did have a crush on Lilly. He had been looking at her, although obviously a little too openly. Not that he was going to tell his sister about it._

_"You're imagining things," he told her, forcing a laugh, making it sound like that was the most ridiculous thing he had ever heard._

_She eyed him suspiciously, but decided to let it go. "Okay," she drawed out, skeptically as she got off of him. She turned around, and headed up the stairs, into her room._

_As soon as Miley was safely out of ear-shot, he let out a long sigh of relief. His sister was starting to get suspcious. He was going to have to be more carefully around the two of them._

**He remembers the first time he realized he loved her.**

_"Where's Lilly," he asked his sister coolly, internally congratulating himself for being so nonchalant._

_He was working at "Rico's" and Miley was occupying one of the counter stools, but the one Lilly usually occupied, remained empty. _

_"Oh, she's over there," she said as she absentmindedly gestured to her left, not looking up from her strawberry smoothie. _

_As casually as he could, he turned his head in the direction Miley was pointing. When he spotted her, he immediately felt his throat get dry and close up. Lilly was sitting a little ways down the beach, and with her, was a boy he had never seen, and they were sitting dangerously close together._

_"Who is that dude? Her cousin?" he asked Miley, trying to ignore the crack that appeared in his voice, and praying desperately that his sister didn't catch it._

_Still engrossed with her smoothie, she didn't look at him when she replied, "That's Chris, from school. He has a massive crush on Lilly."_

_It was a good thing Miley wasn't looking at her brother when she made that statement, otherwise she would have seen his jaw drop to the floor, and him blinking in shock. _

_Recovering quickly, he collected himself long enough to squeak out, "That's cool."_

_That's what he said, but on the inside, his mind was reeling. He looked pack toward the pair and saw Lilly flirting with Chris. She was hanging on to his every word, playfully touching him, and giggling loudly at his jokes. "That should be me." he thought randomly. _

_His eyes widened. Did he really just think that? He did. He was jealous of Chris because he wanted to be the one with Lilly. _

_He tried to shake the thought from his head. It was a ridiculous notion. She was his little sister's best friend. But he watched them get up from the sand to leave and wrap each other in a hug, and he felt a pang in his heart. And it was then that he realized, he was in love with her._

**He remembers every time he was too scared to tell her. **

"Jackson!" she said loudly, snapping him out of his trance.

"Huh, what?" he asked, completely unaware of what was going on around him. Both she and his sister looked at him like he was completely nuts. Well, they always looked at him like that, but that's beside the point.

"Umm, hello?" his sister questioned sarcastically. "We asked you what you wanted on the pizza, like, three minutes ago. But you were off in cuckoo-land."

"Yeah, Jackson," she said to him, shrugging her blonde hair off her shoulders. "What were you thinking about anyway?" she asked.

It was a innocent and valid question, but he couldn't stop the blush from rising in his cheeks. "I...uh, I..." he stammered, trying to stall for time while racking his brain for an appropriate answer. Finally he simply told her, with an uneasy smile on his face, "I, uh... I can't remember."


	2. Chapter 2

**A/N:** Okay, so I decided to change this to a two-shot based on Sidhe-Anomaly's request that I write the part where Jackson actually tells Lilly how he feels. So here it is! Hope you guys enjoy! Feedback is always appreciated. Like the previous chapter, this one is mostly written in italics because it was again, mostly all flashbacks.

**Disclaimer:** Again, I don't own Hannah Montana. Also, I used a quote from Grey's Anatomy in the first section of this chapter. (indicated by parentheses) I don't own those words. Also, the song used in the chapter, again, not mine. It is by Snow Partol. Thanks!

* * *

**He remembers the first time he told her how he felt about her.**

_It wasn't something he had planned. Well, okay, he had always planned on telling her. But whenever he thought too deeply about it, he would freeze up, get nervous, and chicken out. So one day, he just blurted it out ,without even thinking. _

_There was nothing particularly special about that day at the time, but little did he know, it was about to become a day he would always remember. _

_Jackson had been working at Rico's that day, as usual, and Miley and Lilly were at the beach "scoping out the guys", their words, not his. Anyway, it was a slow day, there were no customers at his stand. Then, he saw her coming. To any ordinary passerby, she would have looked like any normal beach-going teenager. She was wearing long, black, surfer shorts and a pink bikini top, her blonde hair in loose braids. But to Jackson, she was beautiful. She always looked beautiful._

_She walked right up to the counter and sat down at her usual stool. "'Sup, Jackson?" she asked casually, picking up a menu, looking it over._

_Before he could stop himself, the words flew right out of his mouth. "I think I love you," he told, staring right at her._

_He couldn't see her reaction, the over-sized menu hiding her from view. However, a peal of laughter escaped from behind it. "Shut up, you're not as funny as you think you are," she said, laughing, fully expecting him to make some wise-ass remark back._

_However, he just gently pulled the menu from her grip, leaving her hands wrapped in fists on the counter. She glanced up at him, but he couldn't bring himself to look at her. He zoned out, the reality of what he had just said hitting him like a ton of bricks. _

_Then she spoke up. "Jackson," she began, her voice soft and shaky. "Stop messing around,"_

_He looked down, his eyes finally locking in with hers."Do you want to go to dinner with me tonight?"_

_"Why are you doing this?" she asked her voice now sounding really worried. Not that he blames her. She had never seen him as anything other than Miley's goofy older brother who reminded her of some stupid baby lion cub._

_So he decided to just let it all out, the words flowing from his mouth like a river, "You know, I've been wanting to say this for a while now, Lilly. I have a huge, massive, gigantic, undeniable crush on you," he confessed. _

_She opened her mouth to speak, but he cut her off. "No, let me get this out. I figure this is already humiliating enough, might as well top it off, right?" _

_She closed her mouth and allowed him to continue. "Actually, you know what? I don't have a crush on you. I'm in love with you. And as crazy as that sounds, it's true. I love everything about you. I love the way you're always at our house. I love the way you always come into our house on your skateboard. I love your goofy hats. I love the way you kink your eyebrow when you look at me when I'm being an idiot. So I guess what I am trying to say is that I love you, Lilly Truscott. (In a really, really, big pretend to like your taste in music, let you eat the last piece of cake, stand outside with a radio over my head unfortunate way)," he concluded, baring his entire heart and soul to her. _

_She studied him, expressionless. He was worried about what her reaction would be when he finally told her, but somehow no reaction was worse than a bad reaction._

_"Jackson, I...I don't know what to say," she said breathlessly. _

_That was all he needed to hear. "It's okay. You don't have to say anything. I just had to get that off my chest," he said, turning around to go to the back of the shop._

_He stopped short when he felt something hit him in the back of his head. Looking around, he saw a crumbled up piece of paper lying at his feet. He bent down and retrieved it. When he opened it, on it was written one simple word: "yes."_

_He turned around to look at Lilly, who was once again studying the menu, her faced flushed._

_"What's this?" he asked slowly._

_"Yes. I'd love to go to dinner with you tonight," she said with a bright smile, never tearing her eyes off the menu._

_His own face was taken over by a grin, and he continued to the back of Rico's with a feeling that that day would be the beginning of something great. _

**He remembers the first time he went on a date with her.**

_He had a plan. He was going to hurry down the stairs and out the front door before either his dad or his sister had a chance to question where he was going. He tiptoed quietly down the stairs. So far so good. He carefully made his way over to the door. Almost there. He reached for the door knob, which let out a creaky "SQUEAK" as he turned it. Busted. _

_Miley came bounding out of the kitchen. She let out a whistle when she caught sight of her brother. He was decked out in his nicest outfit. Non-wrinkled khaki pants and blue polo, and it looked like he had actually ran his hair under some water for once._

_"Dang, Jackson. Got a hot date?" she asked him, completely kidding. _

_He shot her a "look." "Oh my, God! Do you?!" she screeched, running over to her brother, looking him up and down._

_He just smiled humbly. "You do!" she said in amazement. "Who's the poor girl who fell for your cheese-ball lines?" _

_Jackson shot his sister a knowing smile, ruffled her hair like she was five, and slipped out the door, leaving Miley staring at a closed door with her jaw hanging to the floor._

_He picked her up at her house. She, too, had dressed up for the occasion, although her clothes looked like they were slightly too big for her, like she had stolen them out of her older sister's closet._

_The ride to the restaurant was awkward, to put in nicely, after the initial greetings. He concentrated on the road in front of them, jaw clenching every so often while he tried to think of something clever to say. She rested her elbow on the window, and was looking lazily at the passing scenery with her chin resting in her hand. _

_He tried to steal glances at her, trying to read her facial expressions to see what she was thinking. But it was no use. He sighed dejectedly, and they continued onto the restaurant in silence._

_By the time the waiter had left with their orders, he had about all of the awkward silence he could stand._

_"So I went to buy some camouflage pants the other day but I couldn't find any," he blurted out just as she was taking a sip of her soda. _

_She looked at him, her eyebrow kinking, trying to decide if he was being serious. Then her eyes widened as she recognized the joke. Her hand flew to her mouth, but it was too late, soda shot everywhere as she dissolved into a fit of giggles and coughs. _

_"Oh my, God. I am SO sorry," she said with tears in her eyes and soda dripping from her nose. _

_He looked at her trying to suppress his laughter. "I think some of the hit me," he said, his voice cracking up as a couple snickers escaped._

_Her face turned red. "I can feel the bubbles in my nose," she said embarrassed._

_That did it. He lost it. His laughter emitted from him loudly, and she joined him, the ice between the pair, finally broken. There wasn't another awkward silence between them the rest of the night._

**He remembers the first time he danced with her.**

_They sat in the restaurant until they were kicked out because the wait staff wanted to go home. As they reached his car, Jackson turned to her, his eyes shining._

_"Lilly, would you like to dance?" he asked her with a mischievous grin on his face._

_He noticed her eyebrow kinking, which of course meant that she thought he was insane. "In the parking lot?" she questioned skeptically. _

_"Check it out," he said as he opened the driver's side door. He inserted the keys in the ignition and turned the lights on, illuminating a small section of the parking lot. He pushed the radio on, and the sound of "Chasing Cars" by Snow Patrol began emitting from the car. _

_I don't quite know  
How to say  
How I feel _

Those three words  
Are said too much  
But not enough

_He went around back to the front of the car. He took her hand and pulled her close. He snaked his arms around her tiny waist as she wrapped her arms around his neck. At first, she was keeping her distance as there was a good foot between them, but as the song went on, he could feel her gradually moving closer and closer, until she was right up against him, her head resting on his chest, eyes closed._

_They gathered from stares from curious passerbys, but neither of them noticed. They were too wrapped up in their own little world. Then Jackson felt a drop of something wet on his head. Looking up, another one landed in his eye, making him squint. The first few drops of a rainstorm were beginning to fall. Then, without warning, it began to pour._

_Lilly shrieked in surprise, and went to dash for the car. Jackson quickly grabbed her arm and pulled her back to him._

_"Where do you think you're going?" he asked softly. _

_Lilly looked at him and felt herself begin to melt under his gaze. She moved back into the comfortable position against, and the two continued swaying in the pouring rain, floodlighted by the lights of his car._

_If I lay here  
If I just lay here  
Would you lie with me and just forget the world? _

**He remembers the first time he stayed up all night with her.**

_By the time he dropped Lilly off at her house, it was raining even harder. Lilly made a move to get out of the car, but stopped, turning to him._

_"Jackson, come inside. It's too dangerous for you to drive back to your house like this," she stated logically._

_He wanted nothing more than to follow her inside, but he knew the consequences of him staying out any later would not be pretty when he finally went home and faced Robby-Ray._

_"I wish I could, Lilly, but my dad would kill me," he told her regrettably. _

_"So call him and tell him you're at Cooper's house," she argued reasonably._

_"What are we going to tell your mother?" he asked, feeling himself beginning to give into her already._

_She looked at him with a small smile. "My mother's on a business trip for the weekend."_

_Reminding himself that Lilly was still young and he could be arrested in some states for the thoughts he was having at the moment, he slid out of the car and followed her up the walkway and into her house. _

_She lit a fire in the living room, and the two settled on the floor in front of it, with a bag of chips between them. _

_"So, what do you want to do?" she asked him innocently._

_He had a few ideas, but kept those to himself. "We could play the questions game," he suggested, looking at her with an evil smirk._

_"What's that?" she asked._

_"It's a game where I get to ask you three questions and you have to answer them, no matter what, and then you get to ask me three questions," he told her._

_"This could end badly," she muttered softly, helping herself to a chip._

_He laughed. "Don't worry. I'll go easy on you," he said, trying to sound convincing._

_"Why is it that I don't believe you?" she asked, narrowing her gaze at him._

_He slung his arm around her neck. "C'mon. It'll be fine. I promise," he said softly, whispering in her ear._

_She gave in, and the two asked each other questions all night, ignoring the three question limit. Topics ranged from favorite color, to most embarrassing moment. Through it all, Jackson stuck to his promise and made sure that Lilly stayed comfortable. And before they knew it, the clock above them chimed, signaling that it was currently 7 o'clock in the morning._

**He remembers the first time he kissed her. **

_"Oh, man. I can't believe it's 7,"he said with a groan, letting his head fall backward against the couch. _

_"Did you ever call you dad?" she asked him._

_His head shot up, and he looked at her in horror, "Crap," was all he said, looking at her hopelessly._

_"You're really gonna get it," she told him with mock sympathy, reaching up to run her fingers through his sandy-blonde hair. _

_He knew she was right, but somehow, feeling her softly touching him made him feel like it was all going to be okay._

_"It was worth it," he uttered softly, looking deep into her eyes._

_His sudden shift in emotion startled her. She pulled her hand back into her lap. "Jackson? Why are you looking at me like that?"_

_He didn't know how to explain the sudden urge that came over him. All he knew was that he needed to feel her soft lips on his._

_He reached across her and lightly brushed his hand against her cheek. _

_"Jackson, what-?" she began to ask, but was quickly silenced when he pressed his mouth softly against hers. _

_He pulled away, waiting for a reaction. Her eyes were closed, almost as if she were expecting more. They fluttered opened softly, and she looked at him in total shock. "Why did you do that?" she asked him, breathlessly._

_He simply shrugged. "Because I wanted to," he told her honestly._

_She nodded, taking it all in. "Oh, okay," she said quietly, looking down at the floor._

_Suddenly, her eyes shot up, connecting with his. She moved her head closer to his, grabbing his face between his hands. She looked a him for a moment, and then she leaned even closer, capturing his lips with hers._

**He remembers every time he kisses her.**

"Jackson!" she said loudly, snapping him out of his trance.

"Huh, what?" he asked, completely unaware of what was going on around him. Lilly was lookign at him like he was completely nuts. But then again, what else was new?

"Umm, hello?" his girlfriend questioned sarcastically. "I asked you which movie you wanted to see, like, three minutes ago. But you were off in one of your trances."

"Sorry," he muttered, embarrassed that she caught him daydreaming again.

"What were you thinking about anyway?" she asked, shrugging her blonde hair off her shoulders.

He remembers every time she had asked him that question, and how he had never been able to respond. But now, finally, he was able to answer her.

"Just thinking about this," he answered, wrapping her up in his arms and kissing her passionately.


End file.
